Acetic Acid → [1-Cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester

HRID 2180178ノート

反応式

HRID 2180178 の反応式
[CH2:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][C:9]1([C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[CH:2]([CH3:4])[CH3:3].[CH:23]1([CH:26]=O)[CH2:25][CH2:24]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)CCl.CCOC(C)=O>[CH2:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][C:9]1([C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=2)[CH2:10][CH2:11][N:12]([CH2:26][CH:23]2[CH2:25][CH2:24]2)[CH2:13][CH2:14]1)[CH:2]([CH3:4])[CH3:3]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68534266[4-(4-Iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester

生成物 1

HCID 68533264[1-Cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester収率 95%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of [4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester (0.058 g, 0.14 mmol) in ClCH2CH2Cl (0.75 mL) at room temperature under Ar was added cyclopropanecarboxaldehyde (0.012 mL, 0.156 mmol, 1.2 eq.) and HOAc (0.075 mL, 1% v/v). The mixture was stirred for 0.5 h then Na(OAc)3BH (0.041 g, 0.2 mmol, 1.5 eq.) was added. The mixture was stirred for 16 h, diluted with EtOAc (10 mL) and washed with saturated aqueous NaHCO3 solution (10 mL) and saturated brine (10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated by rotary evaporation to give [1-cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester (0.061 g, 95%). MS (ESI): 471.2/472.2 (M+1).

後処理

  1. stirringThe mixture was stirred for 16 h
  2. washwashed with saturated aqueous NaHCO3 solution (10 mL) and saturated brine (10 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-80f1b748a94744599a9a9407eacaa0f0
出典データセット
uspto-grants-2005_05
特許番号
US06887889B2

反応ノート

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